The Berkshires Vacation Homes

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Featured Vacation Homes in The Berkshires

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in The Berkshires

    Hotel Downstreet

    Hotel Downstreet

    40 Main St, North Adams, MA
    The price is $144 per night from Dec 24 to Dec 25
    $144
    includes taxes & fees
    $129 per night
    Dec 24 - Dec 25
    8.6/10 Excellent! (1,000 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    The price is $108 per night from Dec 29 to Dec 30
    $108
    includes taxes & fees
    $97 per night
    Dec 29 - Dec 30
    9/10 Wonderful! (1,001 reviews)
    The Red Lion Inn

    The Red Lion Inn

    30 Main Street, Stockbridge, MA
    The price is $140 per night from Jan 15 to Jan 16
    $140
    includes taxes & fees
    $125 per night
    Jan 15 - Jan 16, 2025
    8.8/10 Excellent! (1,002 reviews)

The Berkshires Vacation Homes

Book vacation homes in The Berkshires
Next time you take a group getaway top The Berkshires, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of The Berkshires vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every The Berkshires vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in The Berkshires; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a The Berkshires rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to The Berkshires is sure to be a winner.

The Berkshires Vacation Homes essential information

Accommodation
253 Vacation Homes
Lowest Price
$108
Highest Price
$223
Popular accommodation
Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Antique Farmhouse Totally Restored , Berkshire Ski House on Lake Garfield w/HT By Great Barrington , Peace and quiet on the lake, Private Estate, Heated YEARROUND Outdoor Pool, Quintessential 6-BR Berkshires Lodge, Amore Estate - beautiful room with many places to explore and relax in., Beautiful Lenox Home, 3 Mi to Shakespeare & Co!